Process for anomerizing nucleosides
First Claim
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1. A process for preparing a beta nucleoside anomer of the formula ##STR3## wherein R1 is hydroxy;
- R2 and R3 are each selected from the group consisting of hydrogen, azide, lower alkyl, fluoro, hydroxy, and OB provided when one of R2 and R3 is hydroxy, the other of R2 and R3 cannot be fluoro, azide or hydroxy;
R4 and R5 are each selected from the group consisting of hydrogen, azide, lower alkyl, fluoro, hydroxy, and OB, where each B is independently a lower alkyl or base-stable hydroxyl protecting group;
provided when one of R4 and R5 is hydroxy, the other of R4 and R5 cannot be fluoro, azide or hydroxy; and
Z is a nucleobase of the formula ##STR4## wherein X is selected from N and CR8 where R8 is hydrogen or lower alkyl;
R6 is selected from the group consisting of amino, lower alkyl amino, di(lower alkyl) amino, acyl amino, and N-acyl lower alkyl amino; and
R7 is selected from the group consisting of hydrogen, lower alkyl, fluoro and lower alkenyl;
comprising contacting an alpha nucleoside of formula ##STR5## with a hydroxide base in an organic solvent.
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Abstract
A process for increasing the amount of a desired anomer nucleoside from an undesired anomeric nucleoside mixture thereof by contacting the mixture with a hydroxide base in an organic solvent.
54 Citations
43 Claims
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1. A process for preparing a beta nucleoside anomer of the formula ##STR3## wherein R1 is hydroxy;
- R2 and R3 are each selected from the group consisting of hydrogen, azide, lower alkyl, fluoro, hydroxy, and OB provided when one of R2 and R3 is hydroxy, the other of R2 and R3 cannot be fluoro, azide or hydroxy;
R4 and R5 are each selected from the group consisting of hydrogen, azide, lower alkyl, fluoro, hydroxy, and OB, where each B is independently a lower alkyl or base-stable hydroxyl protecting group;
provided when one of R4 and R5 is hydroxy, the other of R4 and R5 cannot be fluoro, azide or hydroxy; and
Z is a nucleobase of the formula ##STR4## wherein X is selected from N and CR8 where R8 is hydrogen or lower alkyl;
R6 is selected from the group consisting of amino, lower alkyl amino, di(lower alkyl) amino, acyl amino, and N-acyl lower alkyl amino; and
R7 is selected from the group consisting of hydrogen, lower alkyl, fluoro and lower alkenyl;
comprising contacting an alpha nucleoside of formula ##STR5## with a hydroxide base in an organic solvent. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26)
- R2 and R3 are each selected from the group consisting of hydrogen, azide, lower alkyl, fluoro, hydroxy, and OB provided when one of R2 and R3 is hydroxy, the other of R2 and R3 cannot be fluoro, azide or hydroxy;
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27. A process for preparing an alpha nucleoside anomer of the formula ##STR6## wherein R1 is hydroxy;
- R2 and R3 are each selected from the group consisting of hydrogen, azide, lower alkyl, fluoro, hydroxy, and OB provided when one of R2 and R3 is hydroxy, the other of R2 and R3 cannot be fluoro, azide or hydroxy;
R4 and R5 are each selected from the group consisting of hydrogen, azide, lower alkyl, fluoro, hydroxy, and OB, where each B is independently a lower alkyl or base-stable hydroxyl protecting group;
provided when one of R4 and R5 is hydroxy, the other of R4 and R5 cannot be fluoro, azide or hydroxy; and
Z is a nucleobase of the formula ##STR7## wherein X is selected from N and CR8 where R8 is hydrogen or lower alkyl;
R6 is selected from the group consisting of amino, lower alkyl amino, di(lower alkyl) amino, acyl amino, and N-acyl lower alkyl amino; and
R7 is selected from the group consisting of hydrogen, lower alkyl, fluoro and lower alkenyl;
comprising contacting a beta nucleoside of formula ##STR8## with a hydroxide base in an organic solvent. - View Dependent Claims (28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43)
- R2 and R3 are each selected from the group consisting of hydrogen, azide, lower alkyl, fluoro, hydroxy, and OB provided when one of R2 and R3 is hydroxy, the other of R2 and R3 cannot be fluoro, azide or hydroxy;
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Current AssigneeEli Lilly and Company
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Original AssigneeEli Lilly and Company
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InventorsLeTourneau, Michael E., Britton, Thomas C.
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Primary Examiner(s)Robinson, Douglas W.
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Assistant Examiner(s)WILSON, JAMES O
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Application NumberUS08/176,981Time in Patent Office512 DaysField of Search536/28.52, 536/28.53, 536/28.1, 536/28.2, 536/28.51US Class Current536/28.52CPC Class CodesC07H 19/048 Pyridine radicalsC07H 19/06 Pyrimidine radicals
